ENANTIOSELECTIVE REDUCTION OF PROCHIRAL ARYL KETONES USING A NOVEL CHIRAL AUXILIARY DERIVED FROM A LABDANE DITERPENE

DIEGO A. CIFUENTE AND CARLOS E. TONN

ARKIVOC - ONLINE JOURNAL OF ORGANIC CHEMISTRY

ARKAT USA INC

Año: 2010

1551-7004

A novel chiral 2-methoxy-1,3,2-dioxaborolane derived from 2á,3á-dihydroxycativic acid, a labdane-type diterpene isolated from aerial parts of Baccharis scandens DC., is reported as a highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. labdane-type diterpene isolated from aerial parts of Baccharis scandens DC., is reported as a highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. labdane-type diterpene isolated from aerial parts of Baccharis scandens DC., is reported as a highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. labdane-type diterpene isolated from aerial parts of Baccharis scandens DC., is reported as a highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. labdane-type diterpene isolated from aerial parts of Baccharis scandens DC., is reported as a highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. á,3á-dihydroxycativic acid, a labdane-type diterpene isolated from aerial parts of Baccharis scandens DC., is reported as a highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained. Baccharis scandens DC., is reported as a highly effective chiral auxiliary. This compound has been successfully used in the borane dimethyl sulfide complex-mediated asymmetric reduction of prochiral aryl ketones at room temperature. Very good chemical yields (up to 89%) and high enantioselectivities were obtained.